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An emoticon used to signify sadness, with a bit or sarcasm or cynicism, or humor. It's like saying "tragic, but you get it".

In an online chat, adding a winkfrown:

"Ya, she was really happy to be there,
until she broke her ankle! ;( "
by Tattered Hoody August 10, 2009
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A feat that is impossible to accomplish. And if you do you just look dumb.
Katie just tried to wink-frown at me... and failed.
by Timfimwa April 23, 2008
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